CS270981B1 - 2-isothiocyanatobenzonitrile and method of its production - Google Patents
2-isothiocyanatobenzonitrile and method of its production Download PDFInfo
- Publication number
- CS270981B1 CS270981B1 CS88695A CS69588A CS270981B1 CS 270981 B1 CS270981 B1 CS 270981B1 CS 88695 A CS88695 A CS 88695A CS 69588 A CS69588 A CS 69588A CS 270981 B1 CS270981 B1 CS 270981B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- isothiocyanatobenzonitrile
- water
- synthesis
- production
- thiophosgene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 5
- GDHYPPBFBJXNRE-UHFFFAOYSA-N 2-isothiocyanatobenzonitrile Chemical compound S=C=NC1=CC=CC=C1C#N GDHYPPBFBJXNRE-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims abstract description 5
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 150000003585 thioureas Chemical class 0.000 abstract description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 2-cyanophenyl Chemical group 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Description
a způsobu jeho výroby reakcí anthraniloni trilu s thiofosgenem v inertním organickém rozpouštědle, s výhodou dichlormethanu v přítomnosti vody.
Látka I a způsob její výroby nebyly doposud v literatuře popsány. 3e známo, že příbuzné arylisothiokyanáty lze připravit reakcí arylaminu s thiofosgenem ve vodné suspenzi, resp. emulzi, případně v chloroformovém roztoku v přítomnosti vody (Dyson G. M., George H. 3.,
3. Chem. Soc. 1924, 1702; Oyson G. M., George H. 3., Hunter R. F., 3. Chem. Soc. 1927, 1189; Oyson G. M. Chem. Ind. 30 (1954), 934; Tietze E., Pe- Tersen S,, Oomagk G., Chem. Ber. 86 (1953 ), 314 ).
Nyní bylo nalezeno, že také látku I lze připravit reakcí anthranilonitrolu s thiofosgenem v inertním organickém rozpouštědle, s výhodou dichlormethanu v přítomnosti vody.
Příklad
Ke směsi obsahující roztok 28,7 g (0,25 mol) thioíosgenu v 30 cm^ dichlormethanu a 70 cm^ vody byl během 10 minut přikapán roztok obsahující v 50 cn? dichlormethanu 23,6 g (0,20 mol) anthranilonitrilu, Směs byla intenzívně míchána po dobu 120 až 180 minut za laboratorní teploty. Potom byla organická vrstva oddělena, vysušena a rozpouštědlo oddestilováno.
Rekrystalizací odparku z petroletheru bylo získáno 28,3 g (88,4 %) 2-isothiokyanatobenzonitrilu.
Bílé jehlice, t. tání 60 až 61° C.
Rf (Silufol UV 254, eluováno CHCl-j) 0,833.
IR spektrum (roztok v CHBr-j) : (NCS) 2 070, V* (CN) 2 240, Y (C = C) 1 595, 1 585, 1 495,
1450 cm’1.
2-Isothiokyanatobenzonitri 1 se používá pro syntézu 3-substituovaných 1-(2-kyanfeny1) thiomočovin, které se používají jako reagenty pro syntézu kondenzovaných pyгimidinových heterocyklů, využívaných ve farmakologii a v zemědělství.
Claims (2)
1. 2-Isothiokyanatobenzonitril I (l).
CS 270 981 81
2-. Způsob výroby 2-isothiokyanatobenzonitrilu I, vyznačený tím, že se ponechá reagovat anthranilonitrii s thiofosgenem v roztoku inertního organického rozpouštědla, s výhodou dichlormethanu v přítomnosti vody za laboratorní teploty.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS88695A CS270981B1 (en) | 1988-02-04 | 1988-02-04 | 2-isothiocyanatobenzonitrile and method of its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS88695A CS270981B1 (en) | 1988-02-04 | 1988-02-04 | 2-isothiocyanatobenzonitrile and method of its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS69588A1 CS69588A1 (en) | 1990-01-12 |
| CS270981B1 true CS270981B1 (en) | 1990-08-14 |
Family
ID=5339539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS88695A CS270981B1 (en) | 1988-02-04 | 1988-02-04 | 2-isothiocyanatobenzonitrile and method of its production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS270981B1 (cs) |
-
1988
- 1988-02-04 CS CS88695A patent/CS270981B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS69588A1 (en) | 1990-01-12 |
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